Ask Dr. Nerdlove by Harris O'Malley

How Can I Date More Than One Woman At A Time?

DEAR DR. NERDLOVE: I tend to meet women on Tinder and date a couple at a time. Five years ago, I did this because while I could be charming for a date or two, soon enough the realities of my then pathetic life would shine through. The reaction was girls tended to like me less the more they got to know me. Most ghosted me within a month. To counter this endless loss, I kept a steady stream of new dates coming.

My life is a lot better now. I have a job, am no longer chronically ill. I am also in therapy to work on myself. That has affected my dating life. Just as before, I meet women online and it goes pretty well. The big difference is that right around the 3-5th date mark, when they’d normally show diminishing signs of interest, women are instead sticking around. If anything, I can tell they like me more and more. This makes me happy in general, but has led to some new problems.

I currently am dating three women and occasionally go on other Tinder dates. None of these girls know about one another. Each relationship is “real” in that we go on dates and hold hands and all that, but none have escalated much emotionally.

I’ve never told any of them I love them, and I certainly never said to any of them we were exclusive. I keep expecting one or all to bring it up, but they never do. I have no idea If they are seeing other guys or if they think we’re monogamous. I feel like had I met them knowing they weren’t gonna bail, I would have been more honest earlier.

I’m aware the easy answer is “just ask them!” But I really don’t want to. If one does ask me, I plan to be honest but vague with them (“I like you a lot, but I’m not interested in monogamy. I don’t expect you to follow any rules, either.”) I’m perfectly fine with a don’t ask don’t tell arrangement. But I worry that if I bring this up myself , I’ll make things awkward or tank a relationship I like.

I don’t have much of a game plan because this is all new to me. I like all three girls, but if any found out and forced me to either date just them or end the relationship, I would end the relationship. I’m coming to believe I will never want monogamy. If anything, I suspect I’d be happiest with a “real” wife or girlfriend that 98% of the time we would look normal. The caveat being we both date/bang other people.

It’s hard to consider myself some cheating playboy because there’s no lie. I certainly wasn’t cheating when we’ve known each other for two weeks. Or a month. But it’s like month six now and it feels like a line has been crossed. Has it? Who decides that and when? If this all ends in disaster, I won’t feel like a scumbag, but I will feel bad for hurting a girl’s feelings.

Interested in your thoughts,

Three’s Company

DEAR THREE’S COMPANY: First of all TC: congratulations on all the progress you’ve been making. You’ve come a long way, and your determination is admirable. You should be proud of everything you’ve achieved; it’s taken a lot of hard work to get there and that’s amazing. In fact, that progress is precisely why you are dealing with what we in the dating advice business call “a quality problem to have”. There are far worse things in this world than to have reached a point where your problem is that you’re having to juggle multiple relationships.

Now with all that being said, let’s talk a little about some best practices when it comes to dating multiple people… and where you’re inadvertently tripping yourself up.

The first issue is how much you may be borrowing trouble from the future. Right now, you’re going on dates and “holding hands and all that”. If I’m perfectly honest, it doesn’t sound like you’re at a point where you’d actually need to worry about how to bring up the “by the way, I’m dating other people” conversation. If holding hands is towards the upper limit of your physical intimacy with these women… well, honestly, I think you’ve got a bit before you have to worry about having any sort of Defining The Relationship conversation. Now if you’re sleeping with these women — whether just one or each of them — then the clock is likely ticking and you’re going to be having these conversations sooner rather than later. But if you haven’t reached that point with them, then I think you’re at a stage where you don’t need to be preoccupied with how to bring it up.

The second issue you’re having is how much you’re letting these relationships “just happen”. Right now, it seems like you’re trying to surf the ambiguity wave, having Schrodinger’s Relationship, where you’re both exclusive and not at the same time and you’ll only know which when she calls the question of “just what are we, anyway?” That’s not the coolest move to pull and one that has a high possibility of ending up with one or more women feeling tricked and upset by the fact that you were dating others. And let’s be real: you know that already. That’s why you’re doing this. You even say it yourself:

But I worry that if I bring this up myself , I’ll make things awkward or tank a relationship I like.

Well… yeah. That’s likely to happen. But hiding something that might be a major dealbreaker because you know that it’s likely going to be the end of the relationship is really not cool. Plus, to be perfectly blunt, it ain’t like it’s going to feel like any less of a betrayal if you hide it for longer.

Now in fairness: I’m a believer that folks should assume non-monogamy and non-exclusivity by default until you’ve had an actual conversation on the subject. While it isn’t fair for someone to try to hold you to an arrangement that you didn’t consent to — or even know that you were involved in — it’s also not cool to let folks assume that you’re their one and only when they want or expect exclusivity. “Well, you didn’t ask,” may be technically true, but it’s not going to be much of a guard against feeling hurt or betrayed and realizing that they were investing time and energy in a relationship that ultimately wasn’t one that they wanted.

This is why I’m a fan of making sure everyone is on the same page early on, and that you’re both clear on what this relationship is. It doesn’t mean that you need to say “Hey, don’t forget, we’re totally not exclusive”, but it is important to check in on occasion and make sure everyone understands what’s happening — even if it’s just to say “hey, FYI: I’m not monogamous, and I don’t expect you to be either.” The more dates you’ve been on or the more intense your connection is, the more that conversation is going to be called for. It’s one thing if you’ve been out three or four times. It’s another if you’ve been seeing each other regularly for months. You may not have said the words, but with social and cultural mores being what they are, it’s not an entirely unfounded assumption on her part either.

So it’s best to be dating intentionally and actively looking for folks who are at least open to the same things you are… which in this case is non-exclusivity. As a rule of thumb: this is something best brought up by date three, or prior to sex, which ever happens first. While I know some folks believe in disclosure immediately — and that may be more appropriate if you already have a primary partner — giving it a few dates first lets them get to know you as a person instead of the image of a polyamorous or non-monogamous man they have in their head. But it’s still a conversation to have early on so that both of you aren’t wasting your time.

This doesn’t mean that people won’t still get the wrong idea, or only hear what they want to hear, but at the very least, it’s considerate and ethical.

Frankly, leaving it ambiguous until someone else brings it up is a coward’s move. Date with intent, my dude. You’re going to need to be an active participant in the relationship and actually help steer things, or you’re going to keep ending up in places you never wanted to go.

The third issue is that it doesn’t sound like you’ve done much in the way of research about ethical non-monogamy and how to manage open or polyamorous relationships. I would strongly suggest that you start doing your due diligence before getting any more deeply involved with these women. If you’re going to want a non-monogamous commitment, then you need to know exactly what that entails and how to maintain it.

So here’s your homework: check out Opening Up by Tristan Taormino, The Ethical Slut by Janet Hardy and Building Open Relationships by Dr. Liz Powell (full disclosure: Dr. Powell is a personal friend of mine and has been a guest expert in my column before). Read these and start to learn about precisely what it takes to start and manage an open relationship, as well as how to talk to your partner(s) about it.

But I can’t emphasize this enough: if these relationships are progressing to the point of seeing them regularly, these are conversations you’re going to need to have. Leaving it up in the air in hopes that it will never come up is how you get dumped so hard your grandparents divorce retroactively. And hiding it in hopes that you can thread this particular needle without actually discussing it and running the risk of ending a relationship is how you end up in the special hell. You know the one.

Good luck.

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